Benzene, C6H6, can be obtained from crude oil.

1. (a)(i)Benzene reacts with bromine, in the presence of a suitable catalyst, forming bromobenzene as one product. Give the name or formula of the other product of this reaction.[1]
2. (a)(ii)In the presence of the catalyst, bromine can be considered to form the electrophile Br⁺. Complete the mechanism by which benzene reacts with Br⁺, using curly arrows to show the movement of electron pairs. [Figure showing incomplete mechanism: Benzene + Br+ → intermediate → Br-benzene + H+][2]
3. (a)(iii)Name this mechanism.[1]
4. (b)(i)Benzene can be used as a starting material in the synthesis of cyclohexylmethanol, C6H11CH2OH, as outlined below. [Figure showing a reaction scheme for the synthesis of cyclohexylmethanol from benzene] Identify a suitable reagent and a suitable catalyst for step 1.[2]
5. (b)(ii)Draw the structure of A. [Figure shows an empty box labeled 'A'][1]
6. (b)(iii)Identify suitable reagents for steps 3 and 4.[2]
7. (b)(iv)Deduce the number of peaks in the carbon-13 NMR spectrum of cyclohexylmethanol.[1]

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